Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles
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Author(s)
Gribble, Michael William
Pirnot, Michael T
Bandar, Jeffrey
Liu, Richard
Buchwald, Stephen Leffler
Date Issued
January 2017
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Gribble, Michael W., et al. “Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles.” Journal of the American Chemical Society, vol. 139, no. 6, Feb. 2017, pp. 2192–95. © 2017 American Chemical Society.
Version
Final published version
Abstract
We report a highly enantioselective CuH-catalyzed Markovnikov hydrosilylation of vinylarenes and vinyl heterocycles. This method has a broad scope and enables both the synthesis of isolable silanes and the conversion of crude products to chiral alcohols. Density functional theory calculations support a mechanism proceeding by hydrocupration followed by σ-bond metathesis with a hydrosilane.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/JACS.6B13029
